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Abstract
The stable carbocation, tri(2-methyl-1-azulenyl)methyl hexafluorophosphate ( 2) was prepared. Steric effect of three 2-methyl groups was investigated by comparison with the 3,3′,3″-trimethyl analogue, tri(3-methyl-1-azulenyl)methyl cation ( 1). Dynamic stereochemistry of 2 was studied by temperature dependent 1H NMR spectra, which were analyzed by flip mechanism. The threshold rotational mechanism for 2 was a two-ring flip in contrast to a one-ring flip for 1, and the activation energies for 2 (18.6 and 17.5 kcal/mol) were higher than for 1 due to increased crowding in the transition state for the rotation.
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